Category: 5414-21-1

Reference of 5414-21-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5414-21-1, name is 5-Bromovaleronitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of m-tolylmagnesium bromide 26, prepared from 416 muL of 3-bromotoluene and 83 mg of magnesium turnings in anhydrous THF (3 mL), was added dropwise under inert atmosphere to a solution of 5-bromovaleronitrile (400 muL, 3.43 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 1 h, quenched with a saturated aqueous solution of NaHCO3 (3 mL) and extracted with dichloromethane (3 * 10 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (dichloromethane/methanol 95:5) to provide the compound 7 as a yellow oil (225 mg, 38% yield). Rf = 0.40 (dichloromethane/methanol 95:5). 1H NMR: delta 1.63-1.71 (m, 2H), 1.79-1.87 (m, 2H), 2.37 (s, 3H), 2.60-2.66 (m, 2H), 3.80-3.86 (m, 2H), 7.18-7.29 (m, 2H), 7.51-7.54 (m, 1H), 7.61-7.62 (m, 1H). 13C NMR: delta 20.0, 21.7, 22.1, 27.4, 50.1, 123.3, 126.8, 128.3, 130.5, 138.1, 140.4, 166.2. MS (ESI) m/z [M+H]+ Calcd for C12H16N+: 174.13. Found: 174.2.

The chemical industry reduces the impact on the environment during synthesis 5-Bromovaleronitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Matera, Carlo; Quadri, Marta; Sciaccaluga, Miriam; Pome, Diego Yuri; Fasoli, Francesca; De Amici, Marco; Fucile, Sergio; Gotti, Cecilia; Dallanoce, Clelia; Grazioso, Giovanni; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 392 – 405;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 5414-21-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5414-21-1, name is 5-Bromovaleronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-bromovaleronitrile (5.12 g, 30.0 mmol) in DMF (40 mL) was added potassium phthalimide (6.00 g, 32.4 mmol). The above suspension was heated at 60 oC for 16 h, concentrated, and partitioned between H20 and DCM. The DCM layer was separated, washed with HA0 (3x) and brine, dried over NA2S04, and concentrated to give the title compound (6.84 g, quantitative yield) as a white solid. 1H NMR (CDC13) : delta 7.87-7. 80 (m, 2H), 7.76-7. 70 (m, 2H), 3.73 (t, 2H, J= 6. 1HZ), 2.43 (t, 2H, J= 7.1 Hz), 1.89-1. 82 (m, 2H), 1.74-1. 67 (m, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromovaleronitrile, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 5414-21-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5414-21-1, name is 5-Bromovaleronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0526] To a stirred solution of [1-(2-(trimethylsilyl)ethoxymethyl)-(1H-benzimidazol-2-ylmethyl)]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (188 mg, 0.455 mmol) and diisopropylethyl amine (0.26 ml<1.49 mmol) in CH3CN was added 5-bromovaleronitrile (0.12 mL, 1.03 mmol). The mixture was heated at 80 C. for 47 hours, after which time the reaction was cooled to room temperature. After removal of volatiles under reduced pressure, the residue was dissolved in CH2Cl2 (20 mL). The solution was washed with brine (3×15 mL). The aqueous phase was extracted with CH2Cl2 (1×15 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure to give a crude orange oil (306 mg). Purification of this oil by column chromatography (1.75 cm OD, 14 g silica, 40:1 CH2Cl2: CH3OH) afforded the purified tertiary amine (110 mg, 50%). [0527] The amine from above (110 mg) was dissolved in ammonia saturated CH3OH(12 mL) and treated with Raney-Nickel (410 mg). The mixture was shaken on a Parr hydrogenator at 50 psi H2 for 20 hours, after which time the mixture was filtered through celite and concentrated to give a crude yellow-orange oil (124 mg). [0528] The amine from above (124 mg) was dissolved in 4N HCl (2 mL) and heated to 50 C. for 6 hours. The mixture was then cooled to room temperature and basified with 10N NaOH (final pH>13). This aqueous phase was extracted with CH2Cl2 (4×10 mL). The organic phase was then dried (Na2SO4), filtered and concentrated to give a crude brown foam (83 mg). Purification of this foam by radial chromatography on silica gel (40:1:1 CH2Cl2: CH3OH: NH4-OH) afforded the pure freebase (38 mg, 46% over two steps). [0529] Using the General Procedure D: Conversion of the freebase from above (38 mg) to the hydrobromide salt gave COMPOUND 50 as a white solid (53 mg, 76%). 1H NMR (D2O) delta 1.14-1.28 (m, 2H), 1.39-1.57 (m, 4H), 1.77-1.90 (m, 1H), 1.96-2.10 (m, 1H), 2.13-2.23 (m, 1H), 2.31-241 (m, 1H), 2.46-2.57 (m, 1H), 2.73-2.90 (m, 3H), 2.96-3.03 (m, 2H), 4.38 (d, 1H, J=16.7 Hz), 4.47-4.57 (m, 2H), 7.60 (dd, 2H, J 6.3, 3.3 Hz), 7.80 (dd, 2H, J=6.2, 3.1 Hz), 7.86 (dd, 11H, J=7.9, 6.0 Hz), 8.31 (d, 1H, J=7.0 Hz), 8.62 (d, 1H, J=4.7 Hz). 13C NMR (D2O) delta 20.40, 23.88, 26.92, 27.63, 27.87, 39.68, 48.51, 52.09, 60.86, 114.26 (2 carbons), 125.85, 126.83 (2 carbons), 131.17, 139.29, 140.47, 147.92 (2 carbons), 151.48, 152.00. ES-MS m/z 364 (M+H) Anal Calc. for C22H29N5 3.1HBr 2.6H2O: C, 39.97; H, 5.69; N, 10.59; Br, 37.46. Found: C, 39.96; H, 5.64; N, 10.62; Br, 37.36.

The synthetic route of 5-Bromovaleronitrile has been constantly updated, and we look forward to future research findings.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5414-21-1, name is 5-Bromovaleronitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

General procedure: A solution of m-tolylmagnesium bromide 26, prepared from 416 muL of 3-bromotoluene and 83 mg of magnesium turnings in anhydrous THF (3 mL), was added dropwise under inert atmosphere to a solution of 5-bromovaleronitrile (400 muL, 3.43 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 1 h, quenched with a saturated aqueous solution of NaHCO3 (3 mL) and extracted with dichloromethane (3 * 10 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (dichloromethane/methanol 95:5) to provide the compound 7 as a yellow oil (225 mg, 38% yield). Rf = 0.40 (dichloromethane/methanol 95:5). 1H NMR: delta 1.63-1.71 (m, 2H), 1.79-1.87 (m, 2H), 2.37 (s, 3H), 2.60-2.66 (m, 2H), 3.80-3.86 (m, 2H), 7.18-7.29 (m, 2H), 7.51-7.54 (m, 1H), 7.61-7.62 (m, 1H). 13C NMR: delta 20.0, 21.7, 22.1, 27.4, 50.1, 123.3, 126.8, 128.3, 130.5, 138.1, 140.4, 166.2. MS (ESI) m/z [M+H]+ Calcd for C12H16N+: 174.13. Found: 174.2.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Electric Literature of 5414-21-1,Some common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Into a four-necked reactor equipped with a thermometer,In a nitrogen stream,5.0 g (30.3 mmol) of 2-hydrazinobenzothiazole was added,Was dissolved in 100 ml of DMF.To this solution were added 20.9 g (152 mmol) of potassium carbonate,5.17 g (30.3 mmol) of 5-bromovaleronitrile was added,And the mixture was stirred at 60 C. for 8 hours.After completion of the reaction,The reaction solution was cooled to 20 C.,The reaction solution was poured into 500 mL of water,And extracted with 500 ml of ethyl acetate.The ethyl acetate layer was dried over anhydrous sodium sulfate.After filtering off sodium sulfate,Ethyl acetate was distilled off under reduced pressure on a rotary evaporator to obtain a yellow solid. This yellow solid was purified by silica gel column chromatography (n-hexane: ethyl acetate = 60: 40) to obtain 3.41 g of Intermediate J (yield: 45.7 mol%) as a white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromovaleronitrile, its application will become more common.

Reference:
Patent; ZEON CORPORATION; SAKAMOTO, KEI; OKUYAMA, KUMI; KIRIKI, SATOSHI; (84 pag.)JP2017/206504; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

5414-21-1, name is 5-Bromovaleronitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C5H8BrN

In a four-neck reactor equipped with a thermometer, in a nitrogen stream, 2-hydrazinobenzothiazole 10.0 g (60.5 mmol) of DMF were dissolved in 100 ml of DMF . To this solution, 41.8 g (304 mmol) of potassium carbonate, And 10.34 g of 5-bromovaleronitrile ( 60.6 mmol), and the whole was stirred at 60 C. for 8 hours. After completion of the reaction, The reaction solution was added to 20 C., and the mixture was poured into 1,000 ml of water, And extracted with 1000 ml of ethyl acetate. After drying the ethyl acetate layer with anhydrous sodium sulfate, Sodium sulfate was filtered off. Ethyl acetate was distilled off from the filtrate under reduced pressure by a rotary evaporator, A yellow solid was obtained. This yellow solid was dissolved in Siri Kagel column chromatography (N-hexane: ethyl acetate = 60: 40) To obtain 6.82 g of Intermediate T as a white solid (yield: 45.7%).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZEON CORPORATION; SAKAMOTO, KEI; OKUYAMA, KUMI; SANUKI, KANAKO; (78 pag.)JP6090514; (2017); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 5414-21-1, These common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

3-(2′-Aminopyrimidin-4′-yl)-1H-indole (80 mg, 0.38 mmol),KOH (30mg, 0.48mmol)With 5-bromopenteronitrile (0.23g, 1.43mmol)Miscible in DMF (6mL),And stirred at 40 C for 15 h,The resulting mixture was concentrated under reduced pressure to about 1/2 volume.Pour into H2O (20 mL),Extracted with EtOAc (15 mL¡Á3).The organic phase was combined and washed with saturated brine (20 mL).Anhydrous Mg2SO4 is dried,Silica gel layer filtration,The filtrate is evaporated to dryness.The resulting solid was dissolved in methanol (10 mL).Dry hydrogen chloride gas was passed at 0 C and stirred for 11 h, then evaporated to dryness.The resulting yellow solid was redissolved in methanol (10 mL).Slowly add 25% concentrated ammonia (1 mL) and stir for 3 h.The mixture is concentrated,Purified by column chromatography,Obtained a yellow solid (89 mg, yield 85%, a compound of formula I-26).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsingtao Ocean Bio-pharmaceutical Institute Co., Ltd.; Jiang Tao; Dong Xueyang; Zhang Lijuan; Tong Sheng; Yin Ruijuan; Zhang Hailin; (26 pag.)CN108218838; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 5414-21-1,Some common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A solution of m-tolylmagnesium bromide 26, prepared from 416 muL of 3-bromotoluene and 83 mg of magnesium turnings in anhydrous THF (3 mL), was added dropwise under inert atmosphere to a solution of 5-bromovaleronitrile (400 muL, 3.43 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 1 h, quenched with a saturated aqueous solution of NaHCO3 (3 mL) and extracted with dichloromethane (3 * 10 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (dichloromethane/methanol 95:5) to provide the compound 7 as a yellow oil (225 mg, 38% yield).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Matera, Carlo; Quadri, Marta; Sciaccaluga, Miriam; Pome, Diego Yuri; Fasoli, Francesca; De Amici, Marco; Fucile, Sergio; Gotti, Cecilia; Dallanoce, Clelia; Grazioso, Giovanni; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 392 – 405;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 5414-21-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5414-21-1 name is 5-Bromovaleronitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Sodium hydride paste (6.16 g. of 61% w/w suspension in liquid paraffin) was added portionwise over 30 minutes to a solution of 3-nitropyrazole (17.4 g.) in dry DMF (150 ml.) with external ice cooling to maintain the temperature at 20-30. The mixture was stirred for 45 minutes and to the almost clear solution was added 5-bromovaleronitrile (25 g.) over 30 minutes, at 25-30, and the mixture was stirred for 4 hours. Water (450 ml.) and EtOAc (450 ml.) were added and the upper layer was separated, dried (MgSO4) and evaporated in vacuo to an oil which was a mixture of 5-(3-nitropyrazol-1-yl)valeronitrile and 5-(5-nitropyrazol-1-yl)valeronitrile. The oil was divided into two 15 g. portions which were fractionated on a silica column (3.5 cm diameter*100 cm long) eluted at 2 atmospheres by EtOAc/60-80 petroleum ether (3:7 v/v). The 1,5 isomer was eluted first followed by the 1,3 isomer. The 5-(3-nitropyrazol-1-yl)valeronitrile had m.p. 32-33. To a solution of 5-(3-nitropyrazol-1-yl)valeronitrile (9.16 g.) in dry THF (200 ml.) was added 5% w/w palladium on carbon (1.8 g.). The mixture was stirred at 20 under an atmosphere of hydrogen. 3.2 Liters of hydrogen were absorbed over 4 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo to give 5-(3-aminopyrazol-1-yl)valeronitrile as an oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromovaleronitrile, and friends who are interested can also refer to it.

Reference:
Patent; ICI Americas Inc.; Imperial Chemical Industries PLC; US4496564; (1985); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5414-21-1, name is 5-Bromovaleronitrile, A new synthetic method of this compound is introduced below., Computed Properties of C5H8BrN

Exemplary compound 10 was prepared according to a synthetic scheme shown in FIG. 2. The synthetic procedures for preparing compound 10 are described in?Probes for Narcotic Receptor Mediated Phenomena. 34. Synthesis and Structure- Activity Relationships of a Potent mu-Agonist d-Antagonist and an Exceedingly Potent Antinociceptive in the Enantiomeric C9-Substituted 5-(3-Hydroxyphenyl)-N-phenylethylmorphan Series?, J. Med. Chem. 2007, 50, 3765-3776.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; RICE, Kenner Cralle; JACOBSON, Arthur E.; LI, Fuying; GUTMAN Eugene S.; BOW, Eric W.; (99 pag.)WO2019/182950; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts